Preparation method for 1,4,5-trisubstituted-2-amino imidazole compound

A technology of aminoimidazole and compound, which is applied in the field of preparation of 1,4,5-trisubstituted-2-aminoimidazole compounds, can solve the problems of poor applicability of different functional groups, cumbersome operation, expensive operation of alkyne and silver nitrate, and achieve The effect of cheap and easy-to-get reaction raw materials, cheap and easy-to-get raw materials, and mild conditions

Inactive Publication Date: 2015-03-04
ZHEJIANG UNIV
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  • Abstract
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AI Technical Summary

Problems solved by technology

[0018] Although the reaction is not difficult to operate, the β-amino-substituted alkyne and silver nitrate used in the reaction are relatively expensive, and the overall cost is high and it is not suitable for large-scale production applications.
[0019] Although there are many reports on the synthesis of 1,4,5-trisubstituted-2-aminoimidazole compounds, the known synthetic methods still have the disadvantages of difficult acquisition of raw materials, low product yield, poor applicability to different functional groups, and relatively high toxicity when used in reactions. Large catalyst, complicated operation and other problems, the above factors make the development of a novel preparation method of 1,4,5-trisubstituted-2-aminoimidazoles a top priority

Method used

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  • Preparation method for 1,4,5-trisubstituted-2-amino imidazole compound
  • Preparation method for 1,4,5-trisubstituted-2-amino imidazole compound
  • Preparation method for 1,4,5-trisubstituted-2-amino imidazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1: Preparation of 5-(4-chlorophenyl)-1-(4-methylphenyl)-4-methyl-1H-imidazol-2-amine

[0046] 1. Raw material 1: Preparation of 3-(4-chlorophenyl)-2-methyl-2-nitrooxirane

[0047] Add 2.8g (20mmol) of p-chlorobenzaldehyde and 9.0ml (100mmol) of nitroethane into the three-necked flask, and slowly add Et 3 N 0.28ml (2mmol). After the addition was complete, stir at room temperature under nitrogen protection for 18h. After the disappearance of raw materials detected by the TLC plate, the excess solvent was evaporated under reduced pressure, and the crude product α-nitroalcohol was directly dissolved in dichloromethane, and then 7.4 mL (42 mmol) of N,N-diisopropylethylamine and formaldehyde were added sequentially. Sulfonyl chloride 1.9 mL (24 mmol), after the addition, the reaction gradually returned to room temperature. After the TLC plate detected that the raw materials disappeared, the reaction system was extracted with dichloromethane, and the organic phase w...

Embodiment 2

[0069] Preparation of Example 2, 5-(4-chlorophenyl)-1-(4-methoxyphenyl)-4-methyl-1H-imidazol-2-amine

[0070] Replace p-methylaniline with p-methoxyaniline, the molar weight is constant, and all the other are the same as in Example 1. 297 mg of the product 5-(4-chlorophenyl)-1-(4-methoxyphenyl)-4-methyl-1H-imidazol-2-amine was obtained as a yellow solid, with a yield of 95%.

[0071] Its structural formula is:

[0072]

[0073] 1 H NMR (500 MHz, CDCl 3 ) δ 7.18 (d, J = 8.5 Hz, 2H), 7.09 (d, J = 8.8 Hz, 2H), 6.94 (d, J = 8.5 Hz, 2H), 6.91 (d, J = 8.8 Hz, 2H), 4.18 (s, 1H), 3.83 (s, 3H), 2.24 (s, 3H). 13 C NMR (126 MHz, CDCl 3 ) 13 C NMR (125MHz, CDCl 3 ) δ 159.21, 148.10 , 132.11, 131.78, 130.04, 129.35, 128.58, 128.56, 128.30, 122.99, 114.95, 55.48, 13.53 HRMS (ESI): m / z calcd for C 17 h 17 ClN 3 O [M+H] + :314.1060, found: 314.1058.

Embodiment 3

[0074] The preparation of embodiment 3, 5-(4-chlorophenyl)-1-phenyl-4-methyl-1H-imidazol-2-amine

[0075] Replace p-methylaniline with aniline, the molar weight is constant, and all the other are the same as in Example 1. 255 mg of the product 5-(4-chlorophenyl)-1-(4-methoxyphenyl)-4-methyl-1H-imidazol-2-amine was obtained as a yellow solid, with a yield of 90%.

[0076] Its structural formula is:

[0077]

[0078] 1 H NMR (500 MHz, CDCl 3 ) δ 7.44-7.40 (m, 2H), 7.39-7.35 (m, 1H), 7.20-7.14 (m, 4H), 6.93 (d, J = 8.5 Hz, 2H), 4.30 (s, 2H), 2.24 (s, 3H). 13 C NMR (125 MHz, CDCl 3 ) δ 147.8, 135.82, 132.01, 131.92, 130.06, 129.87, 129.05, 128.35, 128.32, 127.29, 122.78, 13.29; HRMS (ESI): m / z calcd for C 16 h 15 ClN 3 [M+H] + :284.0955, found: 284.0951.

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Abstract

The invention provides a preparation method for a 1,4,5-trisubstituted-2-amino imidazole compound. The 1,4,5-trisubstituted-2-amino imidazole compound is generated by reaction of a 2,3-disubstituted-2-nitro oxirane compound and an amine compound which are easily subjected to chemosynthesis and cyanamide at the room temperature. According to the preparation method provided by the invention, the design is reasonable, the raw materials are easily accessible, no auxiliary additives needs to be added, the operation is simple and convenient, and the general formula of the 1,4,5-trisubstituted-2-amino imidazole compound is shown in the description.

Description

technical field [0001] The invention belongs to a synthesis method of compounds, and mainly relates to a preparation method of 1,4,5-trisubstituted-2-aminoimidazole compounds. Background technique [0002] As a class of five-membered aromatic heterocyclic compounds, imidazoles are widely used in many fields such as medicine, pesticides, materials, and fine chemicals. 2-aminoimidazole compounds are an important class of imidazole compounds. As an excellent synthetic building block, they are used in the synthesis of many anti-tumor, anti-bacterial, anti-fungal, anti-viral, anti-inflammatory, anti-histamine and anti-hypertensive drugs It plays a vital role. At the same time, 2-aminoimidazole is also a good synthetic intermediate. A series of reactions can occur through the amino functional group, and various derivatives produced therefrom have a wide range of applications in medicine, pesticides, dyes, etc. [0003] Because of the very important application value of 2-aminoim...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/88
CPCC07D233/88
Inventor 郭晓陈文腾齐维兴陈斌辉黄卫俞永平
Owner ZHEJIANG UNIV
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